Sodium Acetate → 2-Chloro-1-(2-hydroxy-4-methoxymethoxybutyl)-4-nitroimidazole

HRID 856161Notes

Reaction equation

HRID 856161 reaction equation
C([O-])(=O)C.[Na+].[CH3:6][O:7][CH2:8][O:9][CH2:10][CH2:11][CH:12]1[CH2:14][O:13]1.[Cl:15][C:16]1[NH:17][CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[N:20]=1>C(O)C>[Cl:15][C:16]1[N:17]([CH2:14][CH:12]([OH:13])[CH2:11][CH2:10][O:9][CH2:8][O:7][CH3:6])[CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[N:20]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 148626352-(2-Methoxymethoxyethyl)oxiraneHCID 178526855HCID 178526855, compound

Product 1

HCID 230814622-Chloro-1-(2-hydroxy-4-methoxymethoxybutyl)-4-nitroimidazoleYield 78.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium acetate (3.51 g, 42.82 mmol) and 2-(2-methoxymethoxyethyl)oxirane (10.3 g, 77.86 mmol) were added to 2-chloro-4-nitro-1H-imidazole (5.74 g, 38.93 mmol) in ethanol (60 ml), and the resulting mixture was stirred under reflux for 13.5 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the resulting mixture was extracted with methylene chloride. The extract was dried over magnesium sulfate and then concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) and then crystallized from methylene chloride-diisopropyl ether to afford 2-chloro-1-(2-hydroxy-4-methoxymethoxybutyl)-4-nitroimidazole (8.51 g, yield 78%) as a light yellow powder.

Workup

  1. temperatureunder reflux for 13.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe resulting mixture was extracted with methylene chloride
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)
  8. customcrystallized from methylene chloride-diisopropyl ether

Sources & evidence

ORD record
ord-64125e4bd94b416385f41f50b915ff2e
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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